Abstract/Summary

We present the development of a novel, environmentally friendly Finkelstein reaction conducted in ionic liquids, which provides a safer and more efficient alternative to the conventional halide exchange reaction employing sodium bromide in sulfuric acid. By leveraging the unique properties of ionic liquids—including high thermal stability, negligible vapor pressure, and tunable solvation characteristics—this new methodology enables an SN2 mechanism under significantly milder conditions, while achieving superior yields and selectivity. Comparative studies demonstrate that the ionic liquid-mediated process not only minimizes the generation of hazardous byproducts and corrosive waste but also enhances reaction reproducibility and efficiency. The improved safety profile and operational simplicity of this approach render it particularly suitable for incorporation into undergraduate organic chemistry curricula, where it serves as an effective pedagogical tool for illustrating SN2 kinetics, stereochemical inversion, and the principles of green chemistry. The reaction provides excellent yields (up to 93%) with high product purity, as confirmed by NMR and mass spectrometry. Additionally, the method is cost-effective due to the recyclability of ionic liquids and is scalable, offering advantages for both small-scale academic laboratories and larger-scale synthesis. Consequently, this synthetic strategy holds significant promise for broader adoption within the synthetic organic community.